CAS 6104-71-8|N-Desmethylclozapine
| Common Name | N-Desmethylclozapine | ||
|---|---|---|---|
| CAS Number | 6104-71-8 | Molecular Weight | 312.79700 |
| Density | 1.38g/cm3 | Boiling Point | 490.1ºC at 760 mmHg |
| Molecular Formula | C17H17ClN4 | Melting Point | 120-125°C |
| MSDS | ChineseUSA | Flash Point | 250.2ºC |
| Symbol | GHS02, GHS06, GHS08 | Signal Word | Danger |
Names
| Name | N-desmethylclozapine |
|---|---|
| Synonym | More Synonyms |
N-Desmethylclozapine BiologicalActivity
| Description | N-Desmethylclozapine is a dengue virus inhibitor, and an agonist of δ-opioid receptor. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Opioid ReceptorSignaling Pathways >>Neuronal Signaling >>Opioid ReceptorResearch Areas >>Infection |
| In Vitro | The IC50s of N-desmethylclozapine, fluoxetine hydrochloride, and salmeterol xinafoate in Huh-7 cells infected with DENV-2 are 1 μM, 0.38 μM, and 0.67 μM, respectively. The levels of NS3 are reduced in cells treated with all three inhibitors compared to DMSO treatment, suggesting that the inhibitors act at a stage prior to viral protein translation. N-Desmethylclozapine-treated cells show a >75% reduction in negative-strand RNA levels[1]. N-desmethylclozapine exhibits slight agonistic effects on the M1 mAChR, and agonistic properties at the 5-HT1A receptor in the cerebral cortex and hippocampus. This compound also behaves as an agonist at the δ-opioid receptor in the cerebral cortex and striatum[2]. N-desmethylclozapine (3 μM) greatly decreases the outward current in excitatory neurons, but not in inhibitory neurons. In excitatory neurons, N-desmethylclozapine alone is more effective than either clozapine alone or the combination of clozapine and N-desmethylclozapine. The effect of N-desmethylclozapine in excitatory neurons is significantly suppressed by 0.1 μM pirenzepine and 1 μM atropine. N-desmethylclozapine, but not clozapine, suppressed K+ channels via M1 receptors in excitatory cells[3]. N-desmethylclozapine leads to a decrease in TxB2 levels under unstimulated conditions as well as under TSST-1 stimulation. Clozapine, N-desmethylclozapine and CPZ possibly act on neurotransmitter systems via modulation of TxA2 or TxB2 production[5]. |
| In Vivo | N-desmethylclozapine in rat and human at M2 and M4 mAChRs underlying presynaptic modulation of GABA and glutamate release, respectively. In particular, N-desmethylclozapine maybe a M2 mAChR antagonist in the rat but has no activity at this receptor in human neocortex. However, N-desmethylclozapine has an agonistic effect at M4 mAChR in the human but no such effect in the rat neocortex[4]. |
| References | [1]. Medigeshi GR, et al. N-Desmethylclozapine, Fluoxetine and Salmeterol inhibit post-entry stages of dengue virus life-cycle. Antimicrob Agents Chemother. 2016 Aug 29. [2]. Odagaki Y, et al. Comparative analysis of pharmacological properties of xanomeline and N-desmethylclozapine in rat brain membranes. J Psychopharmacol. 2016 Sep;30(9):896-912. [3]. Sugawara Y, et al. Electrophysiological evidence showing muscarinic agonist-antagonist activities of N-desmethylclozapine using hippocampal excitatory and inhibitory neurons. Brain Res. 2016 Jul 1;1642:255-62. [4]. Gigout S, et al. Different pharmacology of N-desmethylclozapine at human and rat M2 and M 4 mAChRs in neocortex. Naunyn Schmiedebergs Arch Pharmacol. 2015 May;388(5):487-96. [5]. Himmerich H, et al. Impact of clozapine, N-desmethylclozapine and chlorpromazine on thromboxane production in vitro. Med Chem. 2012 Nov;8(6):1032-8. |
Chemical & Physical Properties
| Density | 1.38g/cm3 |
|---|---|
| Boiling Point | 490.1ºC at 760 mmHg |
| Melting Point | 120-125°C |
| Molecular Formula | C17H17ClN4 |
| Molecular Weight | 312.79700 |
| Flash Point | 250.2ºC |
| Exact Mass | 312.11400 |
| PSA | 39.66000 |
| LogP | 3.22080 |
| Index of Refraction | 1.709 |
| InChIKey | JNNOSTQEZICQQP-UHFFFAOYSA-N |
| SMILES | Clc1ccc2c(c1)N=C(N1CCNCC1)c1ccccc1N2 |
| Storage condition | Store at RT |
Safety Information
| Symbol | GHS02, GHS06, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H225-H301 + H311 + H331-H370 |
| Precautionary Statements | P210-P260-P280-P301 + P310-P311 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn |
| Risk Phrases | 20/22-36/37/38 |
| Safety Phrases | S22-S36-S45 |
| RIDADR | 3249 |
| WGK Germany | 3 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles42
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| Functional activation of G-proteins coupled with muscarinic acetylcholine receptors in rat brain membranes. J. Pharmacol. Sci. 125(2) , 157-68, (2014) The functional activation of Gi/o proteins coupled to muscarinic acetylcholine receptors (mAChRs) was investigated with the conventional guanosine-5'-O-(3-[(35)S]thio) triphosphate ([(35)S]GTPγS) bind... |
Synonyms
| 3-chloro-6-piperazin-1-yl-5H-benzo[b][1,4]benzodiazepine |
| Normethylclozapine |
| BzATP triethylammonium salt |
| Desmethylclozapine |
| EINECS 200-659-6 |
| Demethylclozapine |
| N-Demethylclozapine |
| MFCD00210189 |
| N-desmethyl clozapine |
| Norclozapine |
